HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 3-Methyl-5-(4-nitrophenoxymethyl)-1,2,4-oxadiazole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Triethylamine hydrochloride | HCID 11130 | — |
| Reactant | (4-Nitrophenoxy)acetic acid | HCID 15720 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 3-Methyl-5-(4-nitrophenoxymethyl)-1,2,4-oxadiazole | HCID 22060445 | 60% |
Reaction Steps
A mixture of 4-nitrophenoxy acetic acid (2.25 g, 11.4 mmole), acetamideoxime, triethylamine hydrochloride (3.85 g, 27.62 mmole), EDCl.HCl (4.37 g, 22.79 mmole) and diisopropylethylamine (7.42 g, 57.40 mmole) in anhydrous THF (250 ml) was refluxed for 18 h. The unhomogenous brown colored reaction mixture was quenched with water and extracted with EtOAc (3×300 mL). The combined organic layers washed successively with aqueous NaHCO3, brine and dried over anhydrous Na2SO4. Removal of solvent and purified by chromatographic purification provided 5-[(4-nitrophenoxy)methyl]-3-methyl-1,2,4-oxadiazole (1.62 g, 60%). 1H NMR (CDCl3): δ 8.24 (d, 2H, J=8.8 Hz), 7.08 (d, 2H, J=8.8 Hz), 5.36 (s, 2H), 2.44 (s, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07060827B2 |
| Source dataset | uspto-grants-2006_06 |
| ORD ID | ord-acc8e722610e426e85169bc9c3d98ee2 |
| Source note | uspto-grants-2006_06 |